2-amino-5-oxo-7,7-dimethyl-spiro[(4H)-5,6,7,8-tetrahydrochromene-4,3'-(3'H)-7'-chloroindol]-(1'H)-2'-one-3-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-amino-5-oxo-7,7-dimethyl-spiro[(4H)-5,6,7,8-tetrahydrochromene-4,3'-(3'H)-7'-chloroindol]-(1'H)-2'-one-3-carbonitrile
• 英文别名: 2-amino-7'-chloro-1',2',5,6,7,8-hexahydro-7,7-dimethyl-2',5-dioxospiro[4H-1-benzopyran-4,3'-[3H]indole]-3-carbonitrile；2-amino-7'-chloro-7,7-dimethyl-2',5-dioxo-1',2',5,6,7,8-hexahydrospiro[chromene-4,3'-indole]-3-carbonitrile；2-amino-7'-chloro-7,7-dimethyl-2',5-dioxo-5,6,7,8-tetrahydrospiro[chromene-4,3'-indoline]-3-carbonitrile；2'-amino-7-chloro-7',7'-dimethyl-2,5'-dioxospiro[1H-indole-3,4'-6,8-dihydrochromene]-3'-carbonitrile
• 化学式: C₁₉H₁₆ClN₃O₃
• 分子量: 369.807
• InChiKey: RPOVNYSVEWNFJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  7-氯靛红 、 5,5-二甲基-1,3-环己二酮 、 丙二腈 在 苄基三乙基氯化铵 作用下， 以 水 为溶剂， 反应 2.0h， 以92%的产率得到2-amino-5-oxo-7,7-dimethyl-spiro[(4H)-5,6,7,8-tetrahydrochromene-4,3'-(3'H)-7'-chloroindol]-(1'H)-2'-one-3-carbonitrile
  参考文献：
  名称：

  一种简单清洁的方法，用于在水介质中合成螺菌毒素的三组分

  摘要：

  具有重要生物学意义的螺毒素平台的简单，有效的一锅三组分合成方法是通过使Isatin，活化的亚甲基试剂和1,3-二羰基化合物在水性介质中反应来进行的。该方法由于其对环境有益的特性，高产量的处理和易于处理而具有很大的价值。

  DOI：

  10.1016/j.tet.2007.06.113

文献信息

• One-Pot Three-Component Synthesis of Spirooxindoles Catalyzed by Hexamethylenetetramine in Water
  作者：Guo-Dong Wang、Xiao-Nan Zhang、Zhan-Hui Zhang

  DOI：10.1002/jhet.994

  日期：2013.1

  convenient, and multicomponent strategy for synthesis of spirooxindole derivatives has been developed. This strategy provides a rapid access to construct a diversity‐oriented library of spirooxindoles by using three simple and readily available isatin, malononitrile or cyanoacetic ester, and 1,3‐dicarbonyl compound catalyzed by hexamethylenetetramine in water.

  已经开发出一种简单，方便和多组分合成螺环吲哚衍生物的策略。通过使用三种简单易得的Isatin，丙二腈或氰基乙酸酯以及六亚甲基四胺在水中催化的1,3-二羰基化合物，该策略可快速构建以螺菌毒素为导向的多样性文库。
• A simple and clean procedure for three-component synthesis of spirooxindoles in aqueous medium
  作者：Song-Lei Zhu、Shun-Jun Ji、Yong Zhang

  DOI：10.1016/j.tet.2007.06.113

  日期：2007.9

  A simple and efficient one-pot three-component synthesis of the biologically important spirooxindoles scaffold was carried out by the reaction of isatin, activated methylene reagent, and 1,3-dicarbonyl compounds in aqueous medium. This method is of great value because of its environmentally benign character, high yield processing, and easy handling.

  具有重要生物学意义的螺毒素平台的简单，有效的一锅三组分合成方法是通过使Isatin，活化的亚甲基试剂和1,3-二羰基化合物在水性介质中反应来进行的。该方法由于其对环境有益的特性，高产量的处理和易于处理而具有很大的价值。
• Efficient and Convenient Polyethylene Glycol (PEG)-Mediated Synthesis of Spiro-oxindoles
  作者：Harshadas Mitaram Meshram、Dachepally Aravind Kumar、Busam Ramalinga Vara Prasad、Palakuri Ramesh Goud

  DOI：10.1002/hlca.200900273

  日期：2010.4

  Polyethylene glycol (PEG) has been reported as an efficient and convenient medium for the three‐component synthesis for spiro‐oxindole.

  据报道，聚乙二醇（PEG）是螺-氧吲哚三组分合成的一种高效便捷的介质。
• An Efficient Method for Multicomponent Synthesis of Spiro[4H-pyran-oxindole] Derivatives Catalyzed by Magnesium Perchlorate
  作者：Chunlei Wu、Runpu Shen、Jianhui Chen、Chunqi Hu

  DOI：10.5012/bkcs.2013.34.8.2431

  日期：2013.8.20

  A simple and efficient method for the synthesis of spiro[4H-pyran-oxindole] derivatives by means of three-component reactions between isatins, malononitrile or ethyl cyano-acetate, and 1,3-dicarbonyl compounds in the presence of catalytic amount of magnesium perchlorate in 50% aqueous ethanol medium has been described.

  一种简单高效的方法已被描述，用于通过三组分反应合成螺[4H-吡喃-喹啉]衍生物，该反应涉及吲哚酮、马来腈或乙基氰乙酸盐，以及含有1,3-二酮化合物，并在50%乙醇水溶液中催化剂为少量高氯酸镁的条件下进行。
• Sodium stearate-catalyzed multicomponent reactions for efficient synthesis of spirooxindoles in aqueous micellar media
  作者：Li-Min Wang、Ning Jiao、Jun Qiu、Jian-Jun Yu、Jin-Qian Liu、Feng-Lou Guo、Ying Liu

  DOI：10.1016/j.tet.2009.10.091

  日期：2010.1

  A new type of Lewis base-surfactant-combined catalyst (LBSC), sodium stearate, was applied as a catalyst in three-component one-pot reaction involving isatin, malononitrile, and 1,3-dicarbonyl compounds to afford the corresponding spirooxindoles derivatives in good yields (91-97%) under aqueous micellar media. (C) 2009 Elsevier Ltd. All rights reserved.